Best Street Style Looks from Milan Fashion Week

From the uptick in cinching effects vis-à-vis dramatic, oversized belts to unexpected combinations, this season is brimming with a myriad of exciting trends straight from the Milan street style set that we can’t wait to wear in the months ahead.

The latest Fall/Winter 2020 Milan fashion week proved to be particularly noteworthy with health threats dominating the headlines. Despite this, neither the shows that debuted their collections nor the street style stars that attended them disappointed this season. 

As the fashion cognoscente descended in Milan to view the latest designer Fall/Winter 2020 collections, the most stylish editors and influencers provided ample dressing inspiration for the season ahead. From the uptick in cinching effects vis-à-vis dramatic, oversized belts to unexpected combinations, this season is brimming with a myriad of exciting trends straight from the Milan street style set that we can’t wait to wear in the months ahead.


Cinched Effect - New Belts

Regardless of any outfit’s pillar pieces, the one that the Milan street style set donned most this season was the oversized belt. The perfect finishing accessory to instantly cinch the waist for a pronounced cinched effect, the belt comes in an amalgam of variations that tap into the haute trend. Long, pleated skirts paired with cardigans and sleek pants and large blazer sare broken up by gilded belts while bulky outerwear is complemented by a large, buckled iterations. One of our favorite looks is a Western-inspired combination anchored by beige pants, an orange, button-down top with golden accents and a woven brown belt with an ovular buckle.


Nouveau Suiting

This season, Milan street style relied on an influx of our fashion favorites elevating traditional suiting by way of avant-garde silhouettes, new styling techniques, and exciting color palettes. Whether it was the combination between traditionally rigid blazer and trouser materiality and sleek leather tops or exciting, novelty motifs that colored the entire ensemble, the stakes were raised at Milan fashion week. Monochromatic looks that hit mid-calf and were styled with high boots lent the trend a new slant that we’ve been loving.


Trendy Toppers - New Jackets

Dramatic shifts in scale and novelty designs turned tried-and-true finishing jackets and evergreen trenches into this season’s hero pieces. The Milan fashion set sported trenches with stylish, scalloped trimmings and cropped jackets that chicly combined with cotton tops that were hyper-styled and offset with hats for a bohemian look

Milan FW Street Style_White Bottega Veneta Dress Bottega Veneta Chunky Chain Link Bag Bottega Veneta Sandals


New Knits

Milan street style refused to compromise fashion for function this season. Long knitted dresses incorporated ultra-modern cuts and rounded out with chain work pieces for a truly contemporary finish in the case of some. For others, traditional subtle, neutral knitted tops were juxtaposed against everything from retro-inspired bowler bags to bright hues and leather accessories for a truly dynamic combination that shook up Milan fashion week.


New Prints

Unique pieces that we saw this past week straight from the streets of Milan fashion week ran the gamut from floral embroidery to a frenzy of prints and astrology-inspired tops. Indeed, this forthcoming season though there will definitely still be an interest in neutral tones and minimalist design, there is an increased interest in pieces that stand out in their own right. 


Luxe Leathers

Leather’s buttery effect instantly reworks classic silhouettes for a standout look that the Milan street style set couldn’t get enough of this season. Flared denim jeans were chicly offset by lace-up, wraparound pumps and paired with leather blazer and top combinations that both elevated the outfit, yet kept it ultra-cool with a sleek finish. Leather culottes also populated Milan fashion week for their minimalist look, which, when juxtaposed against cozy sweaters, made for a perfect on-the-go ensemble.



Always an exciting trend, animalia prints, both loud and subtle, served as a focal point on the streets of Milan. Whether they came in the form of neutral pieces combined with grey trousers and evergreen trenches for a perfectly put together outfit or loud, cheetah-inspired pants that worked with beaded, bright orange bags and purple tops, animalia prints demonstrated an immense range on our favorite Milan street style stars this season. 


Nouveau Prep

A staple trend in the early 2000s, preppy looks are now being reworked for the modern-day fashion enthusiast. Whether it’s Bella Hadid’s pairing of a diamond-checked sweater with a sleek trench and pants, Kaia Gerber’s checked blazer, flared denim, and dad sneaker combo, or a plaid button-down top offset by au courant utilitarian boots, the options are endless when it comes to traditional preppy attire for the upcoming season.


Pops of Color

Bright hues are innately capable of transforming an ordinary look into something standout. Unexpected color combinations — take, for instance, white and orange, different shades of purple, or neon green and brown — came in the form of a myriad of ensembles that inspired us this season. The fashion set chose to incorporate dramatic, perfectly contrived touches of color into everything from suiting looks to athletic-inspired ensembles and ultra-feminine outfits.



For this season’s Milan street style set, the ruffle proved to be the au courant flourish on everything from two-piece sets to dramatic tops — and with reason. Laden with a softness that juxtaposes against traditional tailoring, ruffles are the ultimate clarion call for the return of retro fads as modern-day comebacks. With looks that have pervaded the runways at Milan fashion week for the past few seasons, it’s no wonder why we’re looking at playful and dynamic frills as a trend to master for the upcoming months.

About the Author
Gretty Garcia handles features and special projects at Editorialist, and covers all things from exciting new releases to profiles on prolific figures across multiple industries. After studying at Harvard College, she began working at Editorialist and is now simultaneously pursuing her master’s degree from the Columbia School of Journalism. When she’s not covering this season’s must-have accessories, she’s adding to her book collection or listening to culture podcasts.
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